4-cyano-3-trifluoromethyl-N-(2-hydroxy-3-phenylthio-2-trifluoromethylpropionyl)aniline → 4-cyano-3-trifluoromethyl-N-[2-(-)-camphanoyloxy-3-phenylthio-2-trifluoromethylpropionyl)aniline

HRID 980158ノート

反応式

HRID 980158 の反応式
[C:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10](Cl)=[O:11].[C:14]([C:16]1[CH:38]=[CH:37][C:19]([NH:20][C:21](=[O:36])[C:22]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH2:23][S:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:18][C:17]=1[C:39]([F:42])([F:41])[F:40])#[N:15]>N1C=CC=CC=1>[C:14]([C:16]1[CH:38]=[CH:37][C:19]([NH:20][C:21](=[O:36])[C:22]([O:35][C:10]([CH:2]2[CH2:3][CH:4]3[C:7]([CH3:9])([CH3:8])[C:1]2([CH3:13])[CH2:6][CH2:5]3)=[O:11])([C:31]([F:32])([F:33])[F:34])[CH2:23][S:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:18][C:17]=1[C:39]([F:41])([F:42])[F:40])#[N:15]

参加物

4

反応物 2

HCID 140647544-cyano-3-trifluoromethyl-N-(2-hydroxy-3-phenylthio-2-trifluoromethylpropionyl)anilineHCID 534427834,7,7-Trimethyl-3-bicyclo[2.2.1]heptanecarbonyl chloride

生成物 1

HCID 867412014-cyano-3-trifluoromethyl-N-[2-(-)-camphanoyloxy-3-phenylthio-2-trifluoromethylpropionyl)aniline

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
95 °C

実験手順

(-)-Camphanoyl chloride (4.33 g.) was added portionwise during 5 minutes to a solution of 4-cyano-3-trifluoromethyl-N-(2-hydroxy-3-phenylthio-2-trifluoromethylpropionyl)aniline (5.8 g.) in pyridine (35 ml.) and the mixture was heated at 95° C. for 150 minutes and then evaporated to dryness. Toluene (50 ml.) was added and the mixture was again evaporated to dryness. The residue was dissolved in ethyl acetate (200 ml.) and the solution was washed with water (30 ml.) and then twice with saturated aqueous sodium chloride solution (20 ml. each time), dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue was dissolved in methylene chloride (10 ml.) and the solution was flash chromatographed on silica gel (Merck 9385) using methylene chloride as eluant. There were thus obtained the two disastereoisomers of 4-cyano-3-trifluoromethyl-N-[2-(-)-camphanoyloxy-3-phenylthio-2-trifluoromethylpropionyl)aniline, the less polar isomer having m.p. 121°-123° C. and the more polar isomer having m.p. 140°-143° C.

後処理

  1. customevaporated to dryness
  2. additionToluene (50 ml.) was added
  3. customthe mixture was again evaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate (200 ml.)
  5. washthe solution was washed with water (30 ml.)
  6. dry with materialeach time), dried over magnesium sulphate
  7. customevaporated to dryness under reduced pressure
  8. dissolutionThe residue was dissolved in methylene chloride (10 ml.)
  9. customchromatographed on silica gel (Merck 9385)

出典と根拠

ORDレコード
ord-5d94e0c5298a46e2b7172da9459d8773
出典データセット
uspto-grants-1987_01
特許番号
US04636505

反応ノート

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